Facile synthesis of highly functionalized bicyclo[3.2.1]octanes as potential building blocks for various natural products
作者:Lazaros Hadjiarapoglou、Armin de Meijere、Hans-Jürgen Seitz、Iris Klein、Dietrich Spitzner
DOI:10.1016/s0040-4039(00)76882-1
日期:1994.5
olefination and reduction of the carbonyl group, or deprotonation at the bridgehead C-7 with subsequent alkylation, acylation or aldol reaction, before they are rearranged to the highly functionalized bicyclo[3.2.1]octane derivatives 10, 11, 13, and 17, respectively. The diones 8 can also be further manipulated, e. g. by regioselective Wittig olefination at C-2.
1- alkoxycyclohexadienolates级联环加成2到2-氯-2- cyclopropylideneacetate 4个产率2-alkoxytricyclo [3.2.1.0 2.7辛烷-2,6-二酮8在酸催化下。所述tricyclooctanones 7可进一步阐述,例如通过Wittig烯化和羰基还原,或者去质子化在桥头C-7与随后烷基化,酰化或醛醇缩合反应,它们被重新安排到高度官能化之前双环[3.2.1]辛烷衍生物10,11,13,和17分别。二重奏8 也可以例如通过在C-2处的区域选择性维蒂希烯化来进一步处理。